N-((2-hydroxynaphthalen-1-yl)(4-methoxyphenyl)methyl)ethanethioamide | 1372783-30-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-((2-hydroxynaphthalen-1-yl)(4-methoxyphenyl)methyl)ethanethioamide
• 英文别名: N-[(2-hydroxynaphthalen-1-yl)-(4-methoxyphenyl)methyl]ethanethioamide
• CAS: 1372783-30-6
• 化学式: C₂₀H₁₉NO₂S
• 分子量: 337.442
• InChiKey: AACKLOXWVXYTJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  73.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-甲氧基苄醇 在 choline bisulfate 、 2-hydroxy-N,N,N-trimethyl ethanaminium peroxydisulfate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.75h， 生成 N-((2-hydroxynaphthalen-1-yl)(4-methoxyphenyl)methyl)ethanethioamide
  参考文献：
  名称：

  Choline peroxydisulfate oxidizing Bio-TSIL: triple role player in the one-pot synthesis of Betti bases and gem-bisamides from aryl alcohols under solvent-free conditions

  摘要：

  一锅法合成Betti碱和双酰胺，使用可生物降解的胆碱过硫酸盐。

  DOI：

  10.1039/c4nj02295e

文献信息

• A highly effective and mild protocol for the production of 1-thioamidoalkyl-2-naphthols using 1,3-disulfonic acid imidazolium trifluoroacetate as a dual-functional catalyst
  作者：Mostafa Karami、Abdolkarim Zare

  DOI：10.1515/znb-2018-0001

  日期：2018.5.24

  A solvent-free protocol for the production of 1-thioamidoalkyl-2-naphthols via a one-pot multi-component reaction of arylaldehydes with 2-naphthol and thioacetamide using the ionic liquid 1,3-disulfonic acid imidazolium trifluoroacetate ([Dsim][TFA]) is described. Furthermore, a plausible and attractive mechanism based on the dual functionality of the catalyst is proposed. Because of the dual functionality of [Dsim][TFA] (possessing acidic and basic sites), it is found to be generally highly effective, affording the products in high yields and short reaction times under mild conditions. We claim that this is one of the best protocols for the synthesis of 1-thioamidoalkyl-2-naphthols (in terms of yield, temperature, conditions, and/or the reaction time).

  一个无溶剂的方法，通过芳香醛与2-萘酚和硫代乙酰胺的一锅多组分反应，在离子液体1,3-二磺酸咪唑三氟乙酸盐([Dsim][TFA])的催化下合成1-硫代氨基烷基-2-萘酚。此外，提出了一个基于催化剂双重功能性的合理且有吸引力的机理。由于[Dsim][TFA]具有酸性和碱性位点的双重功能性，它被发现通常非常有效，在温和条件下以高产率和短反应时间提供产物。我们声称这是合成1-硫代氨基烷基-2-萘酚的最佳方法之一(就产率、温度、条件和/或反应时间而言)。
• Highly effective synthesis of 1-thioamidoalkyl-2-naphthols and tetrahydropyridines using a nanostructured silica-based catalyst under mild conditions
  作者：Navid Irannejad-Gheshlaghchaei、Seyed Sajad Sajadikhah

  DOI：10.2174/1386207323666200914092345

  日期：2020.9.14

  Mass spectroscopy. Results: One-pot multi-component condensation of 2-naphthol with arylaldehydes and thioacetamide catalyzed by nano-[DSPECDA][HSO4] under green, mild and solvent-free conditions led to 1-thioamidoalkyl-2-naphthols in high yields. The nanocatalyst was also used for the preparation of functionalized tetrahydropyridines by the one-pot multi-component reaction of anilines, arylaldehydes

  目的和目的：Nano-2-[N',N'-dimethyl-N'-(silica-n-丙基)ethanaminium chloride]-N,N-dimethylaminium bisulfate (nano-[DSPECDA][HSO4])用作一种高效的非均相二氧化硅基纳米结构催化剂，用于合成 1-硫代氨基烷基-2-萘酚和取代的四氢吡啶。 材料与方法：预期产品在温和条件下制备。在这项工作中，合成了三种新型 1-硫代酰胺烷基-2-萘酚和两种新型四氢吡啶衍生物，并通过 IR、1 H 和13 C NMR 和质谱进行了表征。 结果：纳米-[DSPECDA][HSO 4 ] 催化2-萘酚与芳醛和硫代乙酰胺在绿色、温和、无溶剂条件下的一锅多组分缩合反应得到高收率的1-硫代氨基烷基-2-萘酚。该纳米催化剂还用于在无溶剂和温和条件下通过苯胺、芳基醛和乙酰乙酸乙酯的一锅多组分反应制备官能化四氢吡啶。 结论：
• Synthesis of Novel Thioamidoalkyl- and Thiocarbamidoalkyl Naphthols via a Three-Component Condensation Reaction Using Heterogeneous Catalyst of Ferric Hydrogensulfate
  作者：Hossein Eshghi、Gholam Hossein Zohuri、Saman Damavandi

  DOI：10.1080/00397911.2010.526281

  日期：2012.2.15

  heterogeneous catalyst for the one-pot multicomponent reaction of β-naphthol, aromatic aldehydes, and thioamide derivatives to obtain the corresponding thioamidoalkyl naphthols. Various novel thioamidoalkyl naphthols and thiocarbamidoalkyl naphthols were synthesized in good yields from thioacetamide and thiourea. The heterogeneous nature of the catalyst made it reusable for further chemical reactions. GRAPHICAL

  摘要 以硫酸氢铁[Fe(HSO4)3]为合适的多相催化剂，用于β-萘酚、芳香醛和硫代酰胺衍生物的一锅多组分反应，得到相应的硫代酰胺基烷基萘酚。以硫代乙酰胺和硫脲为原料，以良好的收率合成了各种新型硫代氨基烷基萘酚和硫代氨基烷基萘酚。催化剂的多相性质使其可重复用于进一步的化学反应。图形概要
• Condensation of Aryl Aldehydes, 2-naphthol, and Thioacetamide Catalyzed by<i>N</i>-halo Reagents in Neutral Media
  作者：Ardeshir Khazaei、Fatemeh Abbasi、Ahmad Reza Moosavi-Zare、Marzieh Khazaei、M. Hassan Beyzavi

  DOI：10.1002/jccs.201500125

  日期：2015.10

  three‐component, highly efficient and solvent‐free approach for the synthesis of known and new 1‐thioamido‐alkyl‐2‐naphthol derivatives was investigated. This was achieved via a one‐pot condensation by reacting aryl aldehydes, 2‐naphthol, and thioacetamide in the presence of catalytic amount of 1,3,5‐trichloro‐1,3,5‐triazinane‐2,4,6‐trione (TCCA) and 1,3‐dichloro‐5,5‐dimethylhydantoin (DCDMH). Mechanistically

  研究了一种新的三组分，高效且无溶剂的方法，用于合成已知的和新的1-硫代酰胺基烷基-2-萘酚衍生物。这是通过在催化量的1,3,5-三氯-1,3,5-三嗪烷-2,4,6-三酮存在下使芳基醛，2-萘酚和硫代乙酰胺反应进行单锅缩合来实现的（TCCA）和1,3-二氯-5,5-二甲基乙内酰脲（DCDMH）。从机理上讲，有人提出从TCCA和DCDMH中原位产生Cl +离子来催化中性介质中的反应。在介绍的工作中，大多数产品都是首次报告。
• Catalytic application of<i>N</i>,2-dibromo-6-chloro-3,4-dihydro-2<i>H</i>-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide on the synthesis of 1-carbamato-alkyl-2-naphthols and 1-thioamido-alkyl-2-naphthols
  作者：Ardeshir Khazaei、Fatemeh Abbasi、Ahmad Reza Moosavi-Zare

  DOI：10.1080/17415993.2015.1028938

  日期：2015.7.4

  A novel N-bromo sulfonamide reagent, namely N, 2-dibromo-6-chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide, is prepared and employed as a new and highly efficient catalyst for the preparation of 1-carbamato-alkyl-2-naphthol and 1-thioamido-alkyl-2-naphthol derivatives.